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Key West vacation rentals

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Best Key West vacation rentals

Most recommended vacation rentals in Key West

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Colors On White - Key West - Bedroom
Colors On White
Old Town North of Truman
7.4Good(427)
Parking
Free Wi-Fi
Pool
Pet friendly
C$ 397+
Check availability
Hyatt Residence Club Key West, Sunset Harbor - Key West - Building
Hyatt Residence Club Key West, Sunset Harbor
Truman Annex
7.5Good(99)
Free Wi-Fi
Pool
C$ 551+
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Curry House - Room 9 - Key West - Balcony
Curry House - Room 9
Old Town North of Truman
5.8Fair(20)
Free Wi-Fi
Pool
C$ 451+
Check availability
Pescado Penthouse - Key West - Bedroom
Pescado Penthouse
Old Town South of Truman
7.9Good(46)
Free Wi-Fi
Pet friendly
C$ 1,386+
Check availability
Heart of Old Town getaway, perfect romantic retreat - near the action - Key West - Beach
Heart of Old Town getaway, perfect romantic retreat - near the action
Old Town North of Truman
9.1Wonderful(24)
C$ 637+
Check availability
Key West Villas - Key West - Front desk
Key West Villas
Old Town North of Truman
9.7Wonderful(575)
Free Wi-Fi
Pool
C$ 606+
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Fontana ~ Adults Only, Pool Access King Room At Azul Mansion! - Key West - Living room
Fontana ~ Adults Only, Pool Access King Room At Azul Mansion!
Old Town North of Truman
Free Wi-Fi
C$ 533+
Check availability
Downtown dog-friendly cottage-like studio with patio, full kitchen, cable, & AC - Key West - Outdoors view
Downtown dog-friendly cottage-like studio with patio, full kitchen, cable, & AC
Old Town North of Truman
Free Wi-Fi
C$ 470+
Check availability
Key West Condo close to the Ocean. 1 mile to Smathers & 3 miles to Duval St. \n - Key West - Beach
Key West Condo close to the Ocean. 1 mile to Smathers & 3 miles to Duval St. \n
New Town
Free Wi-Fi
Pool
Spa
C$ 784+
Check availability
Curry House - Pool, King Bed & Balcony! Room 7 - Key West - Balcony
Curry House - Pool, King Bed & Balcony! Room 7
Old Town North of Truman
7.7Good(14)
Free Wi-Fi
Pool
C$ 590+
Check availability
Flor De Cana ~ Adults Only, Poolview Queen Room At Azul Mansion! - Key West - Living room
Flor De Cana ~ Adults Only, Poolview Queen Room At Azul Mansion!
Old Town North of Truman
Free Wi-Fi
C$ 555+
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Curry House Room 6 - Key West - Restaurant
Curry House Room 6
Old Town North of Truman
7.8Good(13)
Free Wi-Fi
Pool
C$ 576+
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Sunny Condo with WiFi, Hot Tub, Pool & Tennis - Key West
Sunny Condo with WiFi, Hot Tub, Pool & Tennis
New Town
Free Wi-Fi
Spa
C$ 746+
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Coral Cove #1 By Brightwild - Key West
Coral Cove #1 By Brightwild
Old Town South of Truman
8.4Very good(24)
Pool
C$ 576+
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Rose Lane Villas - Key West
Rose Lane Villas
Old Town North of Truman
8.5Very good(483)
Free Wi-Fi
Pool
Pet friendly
C$ 755+
Check availability
Sunrise Suites Cozumel Suite #112 - Key West
Sunrise Suites Cozumel Suite #112
New Town
7.7Good(62)
Pool
Pet friendly
Spa
C$ 695+
Check availability
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KAYAK’s insights for vacation rentals in Key West

Discover seasonal trends, ideal booking windows, and other data-driven tips to plan your stay in Key West with confidence.

Which month has the cheapest vacation rental rates in Key West?

Vacation rentals are cheapest in Key West in December, with average rates of C$ 604. In comparison, November is the most expensive month, with prices at C$ 1,539.

What is the cheapest day of the week to book a vacation rental in Key West?

Thursday offers the lowest rates in Key West, with an average nightly price of C$ 654. The highest prices are found on Wednesday, with average rates at C$ 913.

How early should you book a vacation rental in Key West?

Book at least 3 days before your stay begins to get the best price for your Key West vacation rental.
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Good to know

Low season

January

High season

February

Average price (weeknight)

C$ 901

Average price (weekend night)

C$ 522
Cheapest month to stay with an average 40% drop in price.
Most expensive month to stay with an average 53% rise in price.
Average Sun - Thu price over the last 2 weeks.
Average Fri & Sat price over the last 2 weeks.

KAYAK's top tips for finding Key West holiday rental deals

  • For those looking for a Key West vacation rental with a pool, consider staying at Banana's Foster Guesthouse. This establishment has an outdoor pool where there is always a lifeguard present to ensure the guests' safety, and they also provide beach chairs where guests are welcome to relax and sip cocktails by the pool.
  • If you are looking to explore and visit famous attraction sites in and around Key West, then consider staying at Old Town Suites, an establishment located close to many attractions nearby, including Oldest House& Garden Museum, South Beach, and Jackson Square.
  • Check-in at Rose Lane Villas anytime you are traveling to Key West on business. Most business travelers prefer this establishment since it is close to the business district and conveniently sits near several dining locations in Key West.
  • If you are visiting Key West for a fun-packed family vacation, consider staying at The Galleria. This establishment sits near Nelson English City Park, where your kids can run around and have some fun in the sun. It is surrounded by many famous family-friendly attraction sites, including the Ernest Hemingway Home and Museum.
  • Do you wish to explore Key West's nightlife? Then consider staying at Bright Condo W/ Homey Feel, Entertainment & Private Parking-Beach Nearby. This condo is centrally located in Key West and has beach access. It sits in Simonton Street, which is one street away from all bars and restaurants of Duval. This establishment is convenient for travelers looking to access the hottest night scenes in the area within walking distance.
  • Pet friendly, beachfront, pool, air-conditioned, internet, and no minors are the most popular vacation rental property amenities in Key West
  • Vacation rentals in Key West are around 72% more expensive than hotels on average. Search here to compare prices for all accommodation types in Key West.
  • The best vacation rental properties in Key West are Studio Blue (9.9, 53 reviews), Casita de Catherine by AvantStay 1 Block to Duval St w Hot Tub (9.8, 32), and Key West Villas (9.7, 575), based on ratings and reviews from real travelers.
  • Mid Town East is the neighborhood in Key West with the most affordable vacation rental properties (58 properties with an average price of C$ 506 per night). By the Beautiful Sea - Key West Beach Front Condo - w Pool Access, Happys Houseboat Key West, and Island Time Gorgeous Condo Steps To The Beach are the most popular rental properties in Mid Town East.
  • If you’re looking for a cheap vacation rental in Key West, you should consider visiting during the low season. The cheapest vacation homes in Key West can be found in January and October.
  • The cheapest night for renting a vacation home in Key West is Thursday. In contrast, the most expensive is Monday.
  • Vacation rentals are a popular choice for both long and short-term stays. KAYAK users usually book their vacation rental in Key West for 9 days.
See more tips

FAQs when booking a vacation home in Key West

  • What types of vacation rentals are available in Key West?

    There are loads of different property types that you can make your vacation home in Key West. You’ll find apartments, boats, cabins, campgrounds, caravans, condos, cottages, houses, vacation villages, homestays, houseboats, lodges, recreational vehicles and villas.

  • Are there any pet-friendly vacation rentals in Key West?

    There are a number of dog and pet-friendly Key West vacation rentals, with around 16% allowing you to bring your pet along with you.

  • How much is a vacation rental in Key West for tonight?

    In the last 72 hours, users have found Key West vacation rentals for tonight for as low as C$ 343. Search here for similar prices

  • What are the most popular Key West neighborhoods to book a vacation rental in?

    Vacation rentals in Old Town North of Truman, Truman Annex and Old Town South of Truman have the most searches on KAYAK. For more information about Key West's different neighborhoods, check out our Key West's City Guide.

  • How can I find vacation rentals near me in Key West?

    Take a look at our vacation rentals map to find the best vacation rental homes near you.

  • Which Key West vacation rental offers outdoor activities?

    If you want to enjoy outdoor activities while away on vacation, consider staying at Key West Villas. The accommodation offers a tennis court along with tennis equipment, including rackets and balls. There is also a trainer always present for anyone wishing to learn the game's rules, with first aid services also available at all times.

  • Which vacation rental provides laundry services?

    Old Town Suites is one of several Key West house rentals that offer laundry services. Book a stay at this establishment to save yourself from the inconvenience of traveling back home with dirty laundry. Moreover, guests with families and business travelers find these services incredibly convenient.

  • Which vacation rentals in Key West offer shuttle services?

    Coconut Palms is one among a couple of Key West vacation rentals that provide complimentary shuttle services. The shuttle will pick you up from the airport, and their services extend to town and some of the famous attractions in Key West. It is convenient for people traveling with kids or visiting Key West for the first time.

  • Which vacation rentals in Key West are pet-friendly?

    If you wish to travel with your furry friend, consider staying at Rose Lane Villas. This vacation rental is one of the few that offer pet accommodations in the Key West. Prior notice will be required if traveling with pets, and charges may also apply. In case of pet-caused damages, you will be charged for repairs.

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Where to stay in Key West?

Our map will help you find the perfect place to stay in Key West by showing you the exact location of each vacation rental.

What Key West vacation rental guests are talking about

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Vacation rentals by topic

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Old Town Suites - Key West
Old Town Suites
Old Town North of Truman
8.1Very good(717)
Parking
C$ 521+
Check availability
Latitude Penthouse Key West - Key West
Latitude Penthouse Key West
Mid Town West
8.7Very good(38)
Parking
C$ 1,010+
Check availability
Hyatt Residence Club Key West, Windward Pointe - Key West
Hyatt Residence Club Key West, Windward Pointe
New Town
9.1Wonderful(1178)
Parking
C$ 617+
Check availability

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Everything you need to know for your stay in Key West

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Hotels near Key West Airport

Key West vacation rental deals. Search for vacation homes, apartments, condos, cabins, cottages, villas and more in Key West. Find cheap vacation homes to rent in Key West. KAYAK searches hundreds of travel sites to help you find and book a vacation rental in Key West that suits you best.

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